N-phenylsulfonyl-N&#39;-triazinylureas

ABSTRACT

N-phenylsulfonyl-N&#39;-triazinylureas of the general formula ##STR1## and the salts of these compounds with amines, alkali metal bases and alkaline earth metal bases or with quaternary ammonium bases, have good selective herbicidal and plant growth regulating properties when applied pre- and postemergence. 
     In the formula 
     R 1  is hydrogen, halogen, nitro, C 1  -C 4  haloalkyl, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, C 2  -C 5  alkenyl or C 1  -C 4  alkoxycarbonyl, 
     R 2  is C 1  -C 3  alkyl or C 1  -C 3  alkoxy, each unsubstituted or substituted by 1 to 3 halogen atoms, 
     R 3  is halogen, hydrogen, --NR 4  R 5 , C 1  -C 3  alkyl, unsubstituted or substituted by 1 to 3 halogen atoms or C 1  -C 4  alkoxy, or is C 1  -C 3  alkoxy, unsubstituted or substituted by methoxy, ethoxy, or 1 to 3 halogen atoms, 
     R 4  is hydrogen or methyl, 
     R 5  is hydrogen, C 1  -C 2  alkyl or methoxy, 
     A is C 1  -C 4  alkylene or C 2  -C 4  alkenylene, each unsubstituted or substituted by C 1  -C 4  alkyl, and 
     Q is cyano or --COB in which B is alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms; phenyl; phenyl substituted with cyano, nitro, halo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, or haloalkyl of 1 to 3 carbon atoms; amino; alkylamino of 1 to 4 carbon atoms; or dialkylamino of 1 to 4 carbon atoms in each alkyl group.

CROSS REFERENCE TO RELATED APPLICATIONS

This is a continuation-in-part of application Ser. No. 458,799 filed onJan. 18, 1983, now U.S. Pat. No. 4,618,363 issued Oct. 21, 1986.

The present invention relates to novelN-phenylsulfonyl-N'-triazinylureas with herbicidal and plant growthregulating properties, to compositions containing these compounds, andto the use of the novel compounds for controlling weeds, in particularselectively, in crops of useful plants, or for regulating and inhibitingplant growth.

The N-phenylsulfonyl-N'-triazinyl-ureas, and salts thereof, have thegeneral formula I ##STR2## wherein R₁ is hydrogen, halogen, nitro, C₁-C₄ haloalkyl, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₂ -C₅ alkenyl or C₁ -C₄alkoxycarbonyl,

R₂ is C₁ -C₃ alkyl or C₁ -C₃ alkoxy, each unsubstituted or substitutedby 1 to 3 halogen atoms,

R₃ is halogen, hydrogen, --NR₄ R₅, C₁ -C₃ alkyl, unsubstituted orsubstituted by 1 to 3 halogen atoms or C₁ -C₄ alkoxy, or is C₁ -C₃alkoxy, unsubstituted or substituted by methoxy, ethoxy, or 1 to 3halogen atoms,

R₄ is hydrogen or methyl,

R₅ is hydrogen, C₁ -C₂ alkyl or methoxy,

A is C₁ -C₄ alkylene or C₂ -C₄ alkenylene, each unsubstituted orsubstituted by C₁ -C₄ alkyl, and

Q is cyano or --COB in which B is alkyl of 1 to 4 carbon atoms, alkoxyof 1 to 4 carbon atoms; phenyl; phenyl substituted with cyano, nitro,halo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms,alkylthio of 1 to 4 carbon atoms, or haloalkyl of 1 to 3 carbon atoms;amino; alkylamino of 1 to 4 carbon atoms; or dialkylamino of 1 to 4carbon atoms in each alkyl group.

Herbicidally active ureas, triazines and pyrimidines are generally knownin the art. Arylsulfamoyl-heterocyclyl-aminocarbamoyl compounds withherbicidal and plant growth-regulating action have recently beendescribed, for example in European patent publication Nos. 1514 and1515, U.S. Pat. No. 4,127,405, German Offenlegungsschrift No. 2 715 786or French patent specification No. 1 468 747.

In the above definitions, alkyl denotes straight-chain or branchedalkyl, e.g. methyl, ethyl, n-propyl, isopropyl, the four isomers ofbutyl, n-amyl, isoamyl, 2-amyl, 3-amyl, n-hexyl or isohexyl.

Alkoxy denotes methoxy, ethoxy, n-propoxy, isopropoxy and the fourbutoxy isomers, and is, in particular, methoxy, ethoxy or isopropoxy.

Alkylthio is e.g. methylthio, ethylthio, n-propylthio, isopropylthio andn-butylthio, with methylthio and ethylthio being preferred.

Examples of alkenyl radicals are vinyl, allyl, isopropenyl, propen-1-yl,buten-1-yl, buten-2-yl, buten-3-yl, isobuten-1-yl, isobuten-2-yl,penten-1-yl, penten-2-yl, penten-3-yl and penten-4-yl, with vinyl, allyland penten-4-yl being preferred.

Halogen in the above definitions by itself and in haloalkyl is fluorine,chlorine and bromine, with fluorine and chlorine being preferred.

Substituted alkyl or alkenyl radicals are those radicals which carry oneor more of the cited substituents, preferably one such substituent.Where these radicals are substituted by halogen atoms, preferablyseveral hydrogen atoms, and optionally even all hydrogen atoms, of thealkyl or alkenyl radicals are replaced by halogen.

Within the definition of alkoxycarbonyl fall such radicals as --COOCH₃,--COOC₂ H₅, --COO--CH(CH₃)₂, --COOCH₂ --CH₂ --CH₃, --COO--(CH₂)₃ --CH₃,--COO--CH₂ --CH(CH₃)₂, --COO--CH(CH₃)--C₂ H₅ and --COO--C(CH₃)₃.

The invention also comprises the salts which the compounds of formula Iare able to form with amines, alkali metal and alkaline earth metalbases or with quaternary ammonium bases.

Preferred salt-forming alkali metal and alkaline earth metal hydroxidesare the hydroxides of lithium, sodium, potassium, magnesium or calcium,most preferably of sodium or potassium.

Examples of suitable salt-forming amines are primary, secondary andtertiary aliphatic and aromatic amines such as methylamine, ethylamine,propylamine, isopropylamine, the four isomeric butylamines,dimethylamine, diethylamine, diethanolamine, dipropylamine,diisopropylamine, di-n-butylamine, pyrrolidine, piperidine, morpholine,trimethylamine, triethylamine, tripropylamine, quinuclidine, pyridine,quinoline and isoquinoline.

Preferred amines are ethylamine, propylamine, diethylamine ortriethylamine, with isopropylamine and diethanolamine being mostpreferred.

Examples of quaternary ammonium bases are, in general, the cations ofhaloammonium salts, e.g. the tetramethylammonium cation, thetrimethylbenzylammonium cation, the triethylbenzylammonium cation, thetetraethylammonium cation, the trimethylethylammonium cation, and alsothe ammonium cation.

Preferred compounds of the formula I are those in which either

(a) R₁ is hydrogen or

(b) R₂ and R₃ together contain at most 4 carbon atoms.

Further preferred compounds of the formula I are those in thich R₁ ishydrogen, and R₂ and R₃ together contain not more than 4 carbon atoms.

Among these last mentioned compounds, those compounds are particularlypreferred in which A is a C₁ -C₂ alkylene bridge, and Q is cyano or C₁-C₄ alkoxycarbonyl.

As a preferred subgroup of the formula I, those compounds also meritattention in which R₁ is hydrogen or chlorine or methyl bound in the5-position, R₂ is methyl or methoxy, R₃ is methyl, methoxy, chlorine,difluoromethoxy, dimethylamino or ethoxy, A is a straight chain orbranched C₁ -C₅ alkylene bridge or a propenylene bridge, and Q is cyano,ethoxycarbonyl, methoxycarbonyl, acetyl, benzoyl, dimethyl-carbamoyl, orisobutyroyl.

Most preferred, however, is the subgroup of compounds of the formula I,wherein R₁ is hydrogen or methyl bound in the 5-position, R₂ is methylor methoxy, R₃ is methyl, methoxy, chlorine, difluoromethoxy ordimethylamino, A is a straight chain or branched C₁ -C₃ alkylene bridgeand Q is cyano, ethoxycarbonyl, methoxycarbonyl, acetyl, benzoyl,dimethylcarbamoyl, or isobutyroyl.

Preferred individual compounds are:

N-(2-cyanomethoxy-phenylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea,

N-(2-cyanomethoxy-phenylsulfonyl)-N'-(4,6-dimethoxy-1,3,5-triazin-1-yl)-urea,

N-(2-cyanomethoxy-phenylsulfonyl)-N'-(4-dimethylamino-6-methoxy-1,3,5-triazin-2-yl)urea,

N-(2-ethoxycarbonylmethoxy-phenylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea,

N-(2-ethoxycarbonylmethoxy-phenylsulfonyl)-N'-(4,6-dimethoxy-1,3,5-triazin-2-yl)urea,

N-(2-acetylmethoxy-phenylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea,

N-(2-benzoylmethoxy-phenylsulfonyl)-N'-(4,6-dimethoxy-1,3,5-triazin-2-yl)urea,

N-[2-(3-methoxycarbonylallyloxy)phenyl-sulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea,

N-(2-methoxycarbonylmethoxy-5-methyl-phenylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin2-yl)ureaand

N-(2-cyanopropyloxy-phenylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.

The process for obtaining the compounds of formula I is carried out inan inert organic solvent.

In a first process, the compounds of the formula I are obtained byreacting a phenylsulfonamide of the formula II ##STR3## wherein A, R₁and Q are as defined for formula I, in the presence of a base, with anN-triazinylcarbamate of the formula III ##STR4## wherein R₂ and R₃ areas defined for formula I.

In a second process, compounds of formula I are obtained by reacting aphenylsulfonylisocyanate of the formula IV ##STR5## wherein A, R₁ and Qare as defined for formula I, optionally in the presence of a base, withan amine of the formula V ##STR6## wherein R₂ and R₃ are as defined forformula I.

In a further process, the compounds of formula I are obtained byreacting a sulfonamide of the formula II above, optionally in thepresence of a base, with an isocyanate of the formula VI ##STR7##wherein R₂ and R₃ are as defined for formula I.

Finally, the compounds of formula I can also be obtained by reacting aN-phenylsulfonylcarbamate of the formula VII ##STR8## wherein A, R₁ andQ are as defined for formula I, with an amine of the formula V above.

If desired, the ureas of formula I can be converted into basic additionsalts with amines, alkali metal hydroxides or alkaline earth metalhydroxides or with quaternary ammonium bases. This conversion is carriedout e.g. by reacting the compounds of formula I with the equimolaramount of a base and removing the solvent by evaporation.

Some of the starting materials of the formulae II, IV and VII are noveland can be prepared by the following methods.

The novel sulfonamides of formula II used as intermediates are obtainedfrom the corresponding anilines by diazotisation and replacement of thediazo group, with sulfur dioxide, in the presence of a catalyst such ascopper(I) chloride, in hydrochloric acid or acetic acid, and reactingthe resultant phenylsulfonyl chloride with ammonium hydroxide solution.

The compounds of formula II can also be obtained by O-alkylation ofhydroxy-phenylsulfonamides with the corresponding halides or sulfuricacid esters or which corresponding activated alkenyl compounds by1,2-addition, or by reaction of ortho-halophenyl-sulfonamides with metalalcoholates.

Ortho-hydroxyphenylsulfonamide or substitutedortho-hydroxyphenylsulfonamides of the formula VIII ##STR9## wherein R₁is as defined for formula I are described as starting materials forspecific sulfonamide representatives of the formula II in Europeanpatent application No. 44807.

The compounds of formula II used as intermediates are novel and havebeen specially developed for the synthesis of compounds of the formulaI. The novel intermediates have the formula II ##STR10## wherein R₁, Aand Q are as defined for formula I.

The phenylsulfonylisocyanates of the formula IV, which are also novel,may be obtained by reacting the sulfonamides of the formula II withphosgene, in the presence of butyl isocyanate in a chlorinatedhydrocarbon, at reflux temperature. Similar reactions are described in"Recent Methods of Preparative Organic Chemistry", Vol. VI, 211-229,Academic Press, New York and London.

The novel N-phenylsulfonylcarbamates of the formula VII are obtained byreacting the sulfonamides of the formula II with diphenyl carbamate inthe presence of a base. Similar processes are described in Japanesepatent specification No. 61 169.

The starting materials of the formulae III, V and VI are known or theymay be prepared by known methods.

Isocyanates of the formula VI may be prepared by reacting amines of theformula V with oxalyl chloride in a chlorinated hydrocarbon as solvent.Amines of the formula V are known and some are commerically available,or they can be prepared by known methods, q.v. "The Chemistry ofHeterocyclic Compounds", Vol. XIV, Interscience Publishers, New York,London.

It is expedient to carry out the reactions for obtaining compounds offormula I in aprotic, inert organic solvents such as methylene chloride,tetrahydrofuran, acetonitrile, dioxan or toluene.

The reaction temperatures are preferably in the range from -20° to +120°C. The reactions are normally slightly exothermic and can be carried outat room temperature. To shorten the reaction time or also to initiatethe reaction it is expedient to heat the reaction mixture briefly toboiling point. The reaction times can also be shortened by addition of afew drops of a base or isocyanate as catalyst.

The final products can be isolated by concentrating the reaction mixtureand/or removing the solvent by evaporation, and by recrystallising ortriturating the solid residue in a solvent in which it is poorlysoluble, such as an ether, an aromatic hydrocarbon or a chlorinatedhydrocarbon.

The compounds of formula I are stable compounds, and no protectivemeasures are required for handling them.

When used in low rates of application, the compounds of formula I havegood selective growth-inhibiting and selective herbicidal propertieswhich make them most suitable for use in crops of useful plants,especially in cereals, cotton, soybeans, maize and rice. In some casesdamage is also caused to weeds which have up to now have only beencontrolled with total herbicides.

In addition, the compounds of formula I have pronounced plant growthregulating properties which can lead to an increase in the yield ofcultivated plants and harvested crops. Further, many compounds offormula I have a plant growth inhibiting action which is dependent onconcentration. The growth of both monocots and dicots is inhibited.

Thus, for example, the compounds of formula I selectively inhibit thegrowth of leguminosae which are frequently planted as cover crops intropical regions, so that, while soil erosion between cultivated plantsis prevented, the cover crops are unable to compete with the cultivatedplants.

In many cultivated plants inhibition of vegetative growth permits moreplants to be sown in a crop area, so that a higher yield may be obtainedper unit of area. A further mechanism of yield increase using growthregulators resides in the fact that nutrients are able increasingly topromote flower formation and fruiting, whilst vegetable growth isrestricted.

Inhibition of the vegetative growth of monocot plants, e.g. grasses orcereals, is sometimes desirable and advantageous. Such a growthinhibition is of economic interest, inter alia, in respect of grasses,as the frequency of cutting in flower gardens, parks, sports fields orroad shoulders can thereby be reduced. Of importance too is theinhibition of growth of herbaceous and ligneous plants on road shouldersand near transmission lines, or generally in areas in which stronggrowth is undesirable.

The use of growth regulators for inhibiting the growth in height ofcereals is also important, as shortening the stalks diminishes orcompletely eliminates the danger of lodging before harvesting. Inaddition, growth regulators are able to bring about a strengthening ofthe stalks in crops of cereals and this too counteracts lodging.

Further, the compounds of formula I are suitable for preventing storedpotatoes from seeding. During winter storage, potatoes often developsprouts which result in shrinkage, weight loss, and rot.

When the compounds of formula I are applied in higher rates ofapplication, all tested plants are so damaged in their development thatthey wither.

The mode of action of these compounds is unusual. Many aretranslocatable, i.e. they are absorbed by the plant and transported toother parts of it where they then deploy their action. The unusualfeature of the compounds is that they do not only take the path throughthe vascular bundle in the ligneous part from the roots to the leaves,but can also be translocated through the sieve tubes in the bast part ofthe leaves back into the roots. Thus, for example, it is possible todamage perennial weeds to the roots by surface treatment. Compared withother herbicides and growth regulators, the novel compounds of theformula I are effective even when used in very low rates of application.

The invention also relates to herbicidal and plant growth-regulatingcompositions which contain a novel compound of the formula I, and alsoto methods of controlling weeds pre- and postemergence and of inhibitingthe growth of monocots and dicots, especially grasses, tropical covercrops and tobacco plant suckers.

The compounds of the formula I are used in unmodified form or,preferably, together with the adjuvants conventionally employed in theart of formulation, and are therefore formulated in known manner toemulsifiable concentrates, coatable pastes, directly sprayable ordilutable solutions, dilute emulsions, wettable powders, solublepowders, dusts, granulates, and also encapsulations in e.g. polymersubstances. As with the nature of the compositions, the methods ofapplication, such as spraying, atomising, dusting, scattering orpouring, are chosed in accordance with the intended objectives and theprevailing circumstances.

The formulations, i.e. the compositions containing the compound (activeingredient) of the formula I and, where appropriate, a solid or liquidadjuvant, are prepared in known manner, e.g. by homogeneously mixingand/or grinding the active ingredients with extenders, e.g. solvents,solid carriers and, where appropriate, surface-active compounds(surfactants).

Suitable solvents are: aromatic hydrocarbons, preferably the fractionscontaining 8 to 12 carbon atoms, e.g. xylene mixtures or substitutednaphthalenes, phthalates such as dibutyl phthalates or dioctylphthalate, aliphatic hydrocarbons such as cyclohexane or paraffins,alcohols and glycols and their ethers and esters, such as ethanol,ethylene glycol monomethyl or monoethyl ether, ketones such ascyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone,dimethyl sulfoxide or dimethyl formamide, as well as epoxidisedvegetable oils such as epoxidised coconut oil or soybean oil; or water.

The solid carriers used e.g. for dusts and dispersible powders, arenormally natural mineral fillers such as calcite, talcum kaolin,montmorillonite or attapulgite. In order to improve the physicalproperties it is also possible to add highly dispersed silicic acid orhighly dispersed absorbent polymers. Suitable granulated adsorptivecarriers are porous types, for example pumice, broken brick, sepolite orbentonite; and suitable nonsorbent carriers are materials such ascalcite or sand. In addition, a great number of preganulated materialsof inorganic or organic nature can be used, e.g. especially dolomite orpulverised plant residues.

Depending on the nature of the compound of the formula I to beformulated, suitable surface-active compounds are nonionic, cationicand/or anionic surfactants having good emulsifying, dispersing andwetting properties. The term "surfactants" will also be understood ascomprising mixtures of surfactants.

Suitable anionic surfactants can be both water-soluble soaps andwater-soluble synthetic surface-active compounds.

Suitable soaps are the alkali metal salts, alkaline earth metal salts orunsubstituted or substituted ammonium salts of higher fatty acids (C₁₀-C₂₂), e.g. the sodium or potassium salts of oleic or stearic acid, orof natural fatty acid mixtures which can be obtained e.g. from coconutoil or tallow oil. Mention may also be made of fatty acid methyl laurinsalts.

More frequently, however, so-called synthetic surfactants are used,especially fatty sulfonates, fatty sulfates, sulfonated benzimidazolederivatives or alkylarylsulfonates.

The fatty sulfonates or sulfates are usually in the form of alkali metalsalts, alkaline earth metal salts or unsubstituted or substitutedammonium salts and contain a C₈ -C₂₂ alkyl radical which also includesthe alkyl moiety of acyl radicals, e.g. the sodium or calcium salt oflignosulfonic acid, of dodecylsulfate or of a mixture of fatty alcoholsulfates obtained from natural fatty acids. These compounds alsocomprise the salts of sulfuric acid esters and sulfonic acids of fattyalcohol/ethylene oxide adducts. The sulfonated benzimidazole derivativespreferably contain 2 sulfonic acid groups and one fatty acid radicalcontaining 8 to 22 carbon atoms. Examples of alkylarylsulfonates are thesodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid,dibutylnaphthalenesulfonic acid, or of a naphthalenesulfonicacid/formaldehyde condensation product. Also suitable are correspondingphosphates, e.g. salts of the phosphoric acid ester of an adduct ofp-nonylphenol with 4 to 14 moles of ethylene oxide or phospholipids.

Non-ionic surfactants are preferably polyglycol ether derivatives ofaliphatic or cycloaliphatic alcohols, or saturated or unsaturated fattyacids and alkylphenols, said derivatives containing 3 to 30 glycol ethergroups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moietyand 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.

Further suitable non-ionic surfactants are the water-soluble adducts ofpolyethylene oxide with polypropylene glycol, ethylenediamine propyleneglycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms inthe alkyl chain, which adducts contain 20 to 250 ethylene glycol ethergroups and 10 to 100 propylene glycol ether groups. These compoundsusually contain 1 to 5 ethylene glycol units per propylene glycol unit.

Representative examples of non-ionic surfactants arenonylphenolpolyethoxyethanols, castor oil polyglycol ethers,polypropylene/polyethylene oxide adducts,tributylphenoxypolyethoxyethanol, polyethylene glycol andoctylphenoxyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitanand polyoxyethylene sorbitan trioleate are also suitable non-ionicsurfactants.

Cationic surfactants are preferably quaternary ammonium salts whichcontain, as N-substituent, at least one C₈ -C₂₂ -alkyl radical and, asfurther substituents, lower unsubstituted or halogenated alkyl, benzylor lower hydroxyalkyl radicals. The salts are preferably in the form ofhalides, methylsulfates or ethylsulfates, e.g. stearyltrimethylammoniumchloride or benzyldi(2-chloroethyl)ethylammonium bromide.

The surfactants customarily employed in the art of formulation aredescribed e.g. in the following publications: "McCutcheon's Detergentsand Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., 1979;Sisley and Wood, "Encyclopedia of Surface Active Agents", ChemicalPublishing Co. Inc., New York, 1964.

The pesticidal formulations usually contain 0.1 to 95%, preferably 0.1to 80%, of a compound of the formula I, 1 to 99.9% of a solid or liquidadjuvant, and 0 to 25%, preferably 0.1 to 25%, of a surfactant.

Preferred formulations are composed in particular of the followingconstituents (%=percentage by weight):

Solutions

active ingredient: 1 to 30%, preferably 5 to 20%

solvent: 99 to 0%, preferably 95 to 0%

surfactants: 0 to 99%, preferably 0 to 95%

Emulsifiable Concentrates

active ingredient: 1 to 20%, preferably 5 to 10%

surfactant: 5 to 30%, preferably 10 to 20%

liquid carrier: 50 to 94%, preferably 70 to 85%

Dusts

active ingredient: 0.1 to 10%, preferably 0.1 to 1%

solid carrier: 99.9 to 90%, preferably 99.9 to 99%

Suspension Concentrates

active ingredient: 5 to 75%, preferably 10 to 50%

water: 94 to 25%, preferably 88 to 30%

surfactant: 1 to 40%, preferably 2 to 30%

Wettable Powders

active ingredient: 0.5 to 90%, preferably 1 to 80%

surfactant: 0.5 to 20%, preferably 1 to 15%

solid carrier: 5 to 95%, preferably 15 to 90%

Granulates

active ingredient: 0.5 to 30%, preferably 3 to 15%

solid carrier: 99.5 to 70%, preferably 97 to 85%.

Whereas commercial products will be preferably formulated asconcentrates, the end user will normally employ dilute formulations. Theformulations can be diluted to a concentration as low as 0.001%. Therates of application are normally 0.01 to 10 kg a.i./ha, preferably0.025 to 5 kg a.i./ha.

The compositions can also contain further ingredients such asstabilisers, antifoams, viscosity regulators, binders, adhesives, aswell as fertilisers or other active compounds, in order to attainspecial effects.

PREPARATORY EXAMPLES EXAMPLE 1 (a)2-(1-Methoxycarbonylethoxy)benzenesulfonamide

34.6 g of 2-hydroxybenzenesulfonamide and 55.3 g of potassium carbonateare added to 800 ml of acetonitrile. With efficient stirring, 33.4 g ofmethyl 2-bromopropionate are added dropwise over 10 minutes and thesuspension is then heated for 5 hours to 45° C. After the reactionmixture has cooled, the precipitated salts are isolated and the filtrateis concentrated in vacuo. The residue is recrystallised from ethanol,affording 41.8 g of 2-(1-methoxycarbonylethoxy)-benzenesulfonamide witha melting point of 140°-142° C.

(b) 2-(1-Methoxycarbonylethoxy)benzenesulfonyl isocyanate

A mixture of 12.9 g of 2-(1-methoxycarbonylethoxy)-benzenesulfonamide,4.9 g of n-butylisocyanate and 0.1 g of diazabicyclooctane and 130 ml ofxylene is refluxed for 30 minutes. Then 10 g of phosgene are passed intothe solution at the same temperature over 90 minutes. Excess phosgene isexpelled with nitrogen and the solution is then cooled and concentratedin vacuo, affording 17.7 g of 2-(1-methoxycarbonylethoxy)benzenesulfonylisocyanate in the form of a brownish oil which can be further usedwithout purification.

(c)N-[2-(1-Methoxycarbonylethoxy)phenylsulfonyl]-N'-(4,6-dimethylpyrimidin-2-yl)urea(compound 104)

With stirring, a solution of 8.8 g of2-(methoxycarbonylethoxy)benzenesulfonyl isocyanate in 40 ml of absolutetetrahydrofuran is adeed dropwise to a solution of 3.1 g of2-amino-4,6-dimethylpyridine and 0.1 g of diazabicyclooctane in 50 ml oftetrahydrofuran. In the course of this addition the temperature of thesolution rises from 20° to 25° C. After stirring for 3 hours at roomtemperature, the solvent is stripped off and the residue is crystallizedfrom ethyl acetate, affording 5.2 g ofN-[2-(1-methoxycarbonylethoxy)phenylsulfonyl)-N'-(4,6-dimethylpyrimidin-2-yl)ureawith a melting point of 200°-203° C.

The intermediates of the formula I and final products of the formula Ilisted in the following tables are obtained in corresponding manner:

                  TABLE 1                                                         ______________________________________                                         ##STR11##                                                                    No.  A                 Q            m.p. °C.                           ______________________________________                                        1    CH.sub.2          CN           192-195°                           2    CH.sub.2          COOC.sub.2 H.sub.5                                                                         119-121°                           3    CH(CH.sub.3)      COOCH.sub.3  140-142°                           4    CH(CH.sub.3)      COOC.sub.2 H.sub.5                                     5    CH.sub.2          COCH.sub.3   153-154°                           6    CH.sub.2          COC.sub.6 H.sub.5                                                                          180-181°                           7    CH.sub.2CH.sub.2  CN                                                     8    CH.sub.2CH.sub.2  COOCH.sub.3                                            9    CH.sub.2CH.sub.2  COC.sub.6 H.sub.5                                      10   CHCH              COCH.sub.3                                             11   CH.sub.2          CON(CH.sub.3).sub.2                                                                        165-166°                           12   CH.sub.2          COC.sub.3 H.sub.7 -i                                                                       109-113°                           13   (CH.sub.2).sub. 3 COOC.sub.2 H.sub.5                                                                         100-101°                           14   CH(C.sub.2 H.sub.5)                                                                             COOC.sub.2 H.sub.5                                                                         105-106°                           15   (O)CH.sub.2CHCH(Q)                                                                              COOCH.sub.3  162-165°                           ______________________________________                                    

                  TABLE 2                                                         ______________________________________                                         ##STR12##                                                                    No.   A            Q           R.sub.1                                                                             m.p. °C.                          ______________________________________                                        20    CH.sub.2     COOCH.sub.3 5-CH.sub.3                                                                          168-169°                          21    CH.sub.2CH.sub.2                                                                           COOCH.sub.3 5-CH.sub.3                                     22    CH.sub.2     CN          5-Cl                                           23    CH.sub.2     COOCH.sub.3 5-F                                            ______________________________________                                    

                                      TABLE 3                                     __________________________________________________________________________     ##STR13##                                                                    No.                                                                              A             Q        R.sub.2                                                                           R.sub.3                                                                             E  m.p. (°C.)                      __________________________________________________________________________    101                                                                              CH.sub.2      CN       CH.sub.3                                                                          CH.sub.3                                                                            CH 175-178°                        102                                                                              CH.sub.2      COOC.sub.2 H.sub.5                                                                     CH.sub.3                                                                          CH.sub.3                                                                            CH 153-154°                        103                                                                              CH.sub.2      COOCH.sub.3                                                                            CH.sub.3                                                                          CH.sub.3                                                                            CH 194-196°                        104                                                                              CH(CH.sub.3)  COOCH.sub.3                                                                            CH.sub.3                                                                          CH.sub.3                                                                            CH 200-203°                        105                                                                              CH(CH.sub.3)  COOCH.sub.3                                                                            CH.sub.3                                                                          OCH.sub.3                                                                           CH 180-182°                        106                                                                              CH(CH.sub.3)  COOCH.sub.3                                                                            CH.sub.3                                                                          OCH.sub.3                                                                           N  165-167°                        107                                                                              CH(CH.sub.3)  COOCH.sub.3                                                                            OCH.sub.3                                                                         OCH.sub.3                                                                           N  163-165°                        108                                                                              CH(CH.sub.3)  COOCH.sub.3                                                                            OCH.sub.3                                                                         OCH.sub.3                                                                           CH                                        109                                                                              CH(CH.sub.3)  COOCH.sub.3                                                                            OCH.sub.3                                                                         N(CH.sub.3).sub.2                                                                   N  175-176°                        110                                                                              CH(CH.sub.3)  COOCH.sub.3                                                                            OCH.sub.3                                                                         Cl    CH                                        111                                                                              CH.sub.2      CN       CH.sub.3                                                                          OCH.sub.3                                                                           CH 168-170°                        112                                                                              CH.sub.2      CN       OCH.sub.3                                                                         OCH.sub.3                                                                           CH 180-181°                        113                                                                              CH.sub.2      CN       CH.sub.3                                                                          OCH.sub.3                                                                           N  188-190°                        114                                                                              CH.sub.2      CN       OCH.sub.3                                                                         OCH.sub.3                                                                           N  188°                            115                                                                              CH.sub.2      CN       OCH.sub.3                                                                         N(CH.sub.3).sub.2                                                                   N  >220°                           116                                                                              CH.sub.2      COOC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                         N(CH.sub.3).sub.2                                                                   N                                         117                                                                              CH.sub.2      COOC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                         OCH.sub.3                                                                           N  157-159°                        118                                                                              CH.sub.2      COOC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                         OCH.sub.3                                                                           CH 160-162°                        119                                                                              CH.sub. 2     COOC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                         CH.sub.3                                                                            CH 164-165°                        120                                                                              CH.sub.2      COOC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                         CH.sub.3                                                                            N  136-137°                        121                                                                              CH.sub.2      COOC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                         OCH.sub.3                                                                           N                                         122                                                                              CH.sub.2      COCH.sub.3                                                                             CH.sub.3                                                                          OCH.sub.3                                                                           CH                                        123                                                                              CH.sub.2      COCH.sub.3                                                                             CH.sub.3                                                                          OCH.sub.3                                                                           N  163-165°                        124                                                                              CH.sub.2      COCH.sub.3                                                                             OCH.sub.3                                                                         OCH.sub.3                                                                           N                                         125                                                                              CH.sub.2      COCH.sub.3                                                                             OCH.sub.3                                                                         OCH.sub.3                                                                           CH                                        126                                                                              CH.sub.2      COCH.sub.3                                                                             OCH.sub.3                                                                         N(CH.sub.3).sub.2                                                                   N                                         127                                                                              CH.sub.2      COC.sub.6 H.sub.5                                                                      OCH.sub.3                                                                         N(CH.sub.3).sub.2                                                                   N                                         128                                                                              CH.sub.2      COC.sub.6 H.sub.5                                                                      OCH.sub.3                                                                         OCH.sub.3                                                                           N                                         129                                                                              CH.sub.2      COC.sub.6 H.sub.5                                                                      OCH.sub.3                                                                         OCH.sub.3                                                                           CH                                        130                                                                              CH.sub.2      COC.sub.6 H.sub.5                                                                      OCH.sub.3                                                                         CH.sub.3                                                                            CH                                        131                                                                              CH.sub.2      COC.sub.6 H.sub. 5                                                                     OCH.sub.3                                                                         CH.sub.3                                                                            N  180-184°                        132                                                                              (CH.sub.2).sub.3                                                                            CN       OCH.sub.3                                                                         CH.sub.3                                                                            N  165°                            133                                                                              CH.sub.2      COOCH.sub.3                                                                            OCH.sub.3                                                                         CH.sub.3                                                                            N  178-179°                        134                                                                              CH.sub.2      COOCH.sub.3                                                                            OCH.sub.3                                                                         N(CH.sub.3).sub.2                                                                   N  186-187°                        135                                                                              CH.sub.2      CON(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                         OCH.sub.3                                                                           CH 144-147°                        136                                                                              CH.sub.2      COC.sub.6 H.sub.5                                                                      OCH.sub.3                                                                         Cl    CH 168-173°                        137                                                                              CH.sub.2      COC.sub.6 H.sub.5                                                                      OCH.sub.3                                                                         N(CH.sub.3).sub.2                                                                   N  200-205°                        138                                                                              CH.sub.2      CON(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                         CH.sub.3                                                                            N  164-166°                        139                                                                              CH.sub.2      COC.sub.3 H.sub.7 -i                                                                   OCH.sub.3                                                                         CH.sub.3                                                                            CH 122-130°                        140                                                                              (CH.sub.2).sub.3                                                                            COOC.sub.2 H.sub.5                                                                     CH.sub.3                                                                          OCH.sub.3                                                                           N  128-130°                        141                                                                              (CH.sub.2).sub.3                                                                            COOC.sub.2 H.sub.5                                                                     CH.sub.3                                                                          OCH.sub.3                                                                           CH                                        142                                                                              (CH.sub.2).sub. 3                                                                           COOC.sub.2 H.sub.5                                                                     CH.sub.3                                                                          OCHF.sub.2                                                                          CH                                        143                                                                              (CH.sub.2).sub.3                                                                            COOC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                         OCH.sub.3                                                                           N                                         144                                                                              (CH.sub.2).sub.3                                                                            COOC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                         OCH.sub.3                                                                           CH                                        145                                                                              CH(C.sub.2 H.sub.5)                                                                         COOC.sub.2 H.sub.5                                                                     CH.sub.3                                                                          OCH.sub.3                                                                           N  118-120°                        146                                                                              CH(C.sub.2 H.sub.5)                                                                         COOC.sub.2 H.sub.5                                                                     CH.sub.3                                                                          OCH.sub.3                                                                           CH                                        147                                                                              CH(C.sub.2 H.sub.5)                                                                         COOC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                         OCH.sub.3                                                                           CH                                        148                                                                              CH(C.sub.2 H.sub.5)                                                                         COOC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                         OCH.sub.3                                                                           N                                         149                                                                              (O)CH.sub.2CHCH(Q)                                                                          COOCH.sub.3                                                                            CH.sub.3                                                                          OCH.sub.3                                                                           N  152-154°                        150                                                                              (O)CH.sub.2CHCH(Q)                                                                          COOCH.sub.3                                                                            CH.sub.3                                                                          OCH.sub.3                                                                           CH                                        151                                                                              (O)CH.sub.2CHCH(Q)                                                                          COOCH.sub.3                                                                            CH.sub.3                                                                          OCHF.sub.2                                                                          CH                                        152                                                                              (O)CH.sub.2CHCH(Q)                                                                          COOCH.sub.3                                                                            CH.sub.3                                                                          OC.sub.2 H.sub.5                                                                    N                                         153                                                                              (O)CH.sub.2CHCH(Q)                                                                          COOCH.sub.3                                                                            CH.sub.3                                                                          CH.sub.3                                                                            CH                                        __________________________________________________________________________

                                      TABLE 4                                     __________________________________________________________________________     ##STR14##                                                                    No.                                                                              A        Q      R.sub.1                                                                           R.sub.2                                                                           R.sub.3                                                                             E  m.p. (°C.)                         __________________________________________________________________________    201                                                                              CH.sub.2 COOCH.sub.3                                                                          5-CH.sub.3                                                                        OCH.sub.3                                                                         N(CH.sub.3).sub.2                                                                   N  192-195°                           202                                                                              CH.sub.2 COOCH.sub.3                                                                          5-CH.sub.3                                                                        OCH.sub.3                                                                         CH.sub.3                                                                            CH 178-180°                           203                                                                              CH.sub.2CH.sub.2                                                                       CN     5-Cl                                                                              CH.sub.3                                                                          CH.sub.3                                                                            N                                            __________________________________________________________________________

FORMULATION EXAMPLES EXAMPLE 2 Formulation Examples for Solid ActiveIngredients of the Formula I (throughout, Percentages are by Weight)

    ______________________________________                                        (a) Wettable powders                                                                            (a)      (b)      (c)                                       ______________________________________                                        active ingredient 20%      60%      0.5%                                      sodium lignosulfonate                                                                           5%       5%       5%                                        sodium laurylsulfate                                                                            3%       --       --                                        sodium diisobutylnaphthalene-                                                                   --       6%       6%                                        sulfonate                                                                     octylphenol polyethylene glycol                                                                 --       2%       2%                                        ether (7-8 moles of ethylene                                                  oxide)                                                                        highly dispersed silicic acid                                                                   5%       27%      27%                                       kaolin            67%      --       --                                        sodium chloride   --       --       59.5%                                     ______________________________________                                    

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording wettablepowders which can be diluted with water to give suspensions of thedesired concentration.

    ______________________________________                                        (b) Emulsifiable concentrate                                                                         (a)     (b)                                            ______________________________________                                        active ingredient      10%     1%                                             octylphenol polyethylene glycol                                                                       3%     3%                                             ether (4-5 moles of ethylene                                                  oxide)                                                                        calcium dodecylbenzenesulfonate                                                                       3%     3%                                             castor oil polyglycol ether                                                                           4%     4%                                             (36 moles of ethylene oxide)                                                  cyclohexanone          30%     10%                                            xylene mixture         50%     79%                                            ______________________________________                                    

Emulsions of any required concentration can be obtained from thisconcentrate by dilution with water.

    ______________________________________                                        (c) Dusts         (a)     (b)                                                 ______________________________________                                        active ingredient  0.1%    1%                                                 talcum            99.9%   --                                                  kaolin            --      99%                                                 ______________________________________                                    

Dusts which are ready for use are obtained by mixing the activeingredient with the carriers, and grinding the mixture in a suitablemill.

    ______________________________________                                        (d) Extruder granulate                                                                            (a)    (b)                                                ______________________________________                                        active ingredient   10%    1%                                                 sodium lignosulfonate                                                                              2%    2%                                                 carboxymethylcellulose                                                                             1%    1%                                                 kaolin              87%    96%                                                ______________________________________                                    

The active ingredient is mixed and ground with the adjuvants, and themixture is subsequently moistened with water. The mixture is extrudedand then dried in a stream of air.

    ______________________________________                                        (e) Coated granulate                                                          ______________________________________                                        active ingredient  3%                                                         polyethylene glycol 200                                                                          3%                                                         kaolin             94%                                                        ______________________________________                                    

The finely ground active ingredient is uniformly applied, in a mixer, tothe kaolin moistened with polyethylene glycol. Non-dusty coatedgranulates are obtained in this manner.

    ______________________________________                                        (f) Suspension concentrate                                                                          (a)     (b)                                             ______________________________________                                        active ingredient     40%     5%                                              ethylene glycol       10%     10%                                             nonylphenol polyethylene glycol                                                                      6%     1%                                              ether (15 moles of ethylene                                                   oxide)                                                                        sodium lignosulfonate  10%    5%                                              carboxymethylcellulose                                                                               1%     1%                                              37% aqueous formaldehyde solution                                                                   0.2%    0.2%                                            silicone oil in the form of a 75%                                                                   0.8%    0.8%                                            aqueous emulsion                                                              water                 32%     77%                                             ______________________________________                                    

The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspensions of anydesired concentration can be obtained by dilution with water.

    ______________________________________                                        (g) Salt solution                                                             ______________________________________                                        active ingredient     5%                                                      isopropylamine        1%                                                      octylphenol polyethylene glycol                                                                     3%                                                      ether (78 moles of ethylene oxide)                                            water                 91%                                                     ______________________________________                                    

BIOLOGICAL EXAMPLES EXAMPLE 3 Preemergence Herbicidal Activity

Plastic pots are filled with expanded vermiculite (density: 0.135 g/cm³,water absorbing capacity: 0.565 1/l). After the non-adsorptivevermiculite has been saturated with an aqueous emulsion in deionisedwater which contains the test compound in a concentration of 70.8 ppm,seeds of the following plants are sown on the surface: Nasturtiumofficinalis, Agrostis tenuis, Stellaria media and Digitaria sanguinalis.The pots are then kept in a climatic chamber at 20° C., an illuminationof about 20 lux and a relative humidity of 70%. During the germinatingphase of 4 to 5 days, the pots are covered with lightpermeable materialand watered with deionised water to increase the local humidity. Afterthe 5th day, 0.5% of a commercial liquid fertiliser (Greenzit®) is addedto the water. The test is evaluated 12 days after sowing and theactivity on the the plants is assessed according to the followingrating:

1: plants have not emerged or are totally withered

2-3: very pronounced activity

4-6: medium activity

7-8: weak activity

9: no activity (as untreated controls).

    ______________________________________                                        Preemergence activity                                                         Concentration of the test emulsion: 70.8 ppm.                                 Test plant                                                                    Compound                                                                              Nasturtium  Stellaria                                                                              Agrostis Digitaria                               ______________________________________                                        101     2           3        2        3                                       102     3           5        5        3                                       104     2           4        3        3                                       105     2           5        2        4                                       113     1           2        1        1                                       114     1           1        1        1                                       115     2           2        1        2                                       131     1           5        2        4                                       138     3           6        4        5                                       ______________________________________                                    

EXAMPLE 4 Postemergence Herbicidal Action (Contact Action)

A number of weeds and cultivated plants, both monocots and dicots, aresprayed postemergence, in the 4- to 6-leaf stage, with an aqueousdispersion of test compound at a rate of application of 0.5 kg a.i./ha,and then kept at 24°-26° and 45-60% relative humidity. The test isevaluated 15 days after treatment. In this test, the herbicidal actionon plants treated with compounds of the formula I is marked incomparison with untreated controls (rating 1 to 5, mainly 1 to 3).

EXAMPLE 5 Growth Inhibition of Tropical Cover Crops

The test plants (Psophocarpus palustris and Centrosema pubescens) arereared until fully grown and then cut back to a height of 15 cm. Theplants are sprayed 7 days later with an aqueous emulsion of the compoundto be tested. The test plants are kept at 70% relative humidity and 6000lux artificial light for 14 hours per day, at day temperature of 27° C.and night temperatures of 21° C. The test is evaluated 4 weeks afterapplication by assessing and weighing the new growth compared withcontrols and by determining the phytotoxicity.

In this test a marked reduction in new growth of the plants treated withcompounds of the formula I is observed (less than 20% of the new growthof untreated control plants).

EXAMPLE 6 Growth Regulation of Soybeans

Soybeans of the "Hark" variety are sown in plastic containers in anearth/peat/sand mixture (6:3:1). The containers are put into a climaticchamber and the plants develop to the 5-6 trefoil leaf stage after about5 weeks by optimum control of temperature, light, fertiliser addition,and watering. The plants are then sprayed with an aqueous mixture of acompound of the formula I until thoroughly wetted. The concentration oftest compound is up to 100 g a.i./ha. Evaluation is made about 5 weeksafter application. Compared with untreated controls, the compounds ofthe formula I markedly increase the number and weight of the harvestedsiliques on the leading shoot.

EXAMPLE 7 Growth Inhibition of Cereals

Summer barley (Hordeum vulgare) and summer rye (Secale) are sown insterilised soil in plastic beakers in a greenhouse and watered asrequired. The cereal shoots are treated about 21 days after sowing withan aqueous spray mixture of a compound of the formula I. Theconcentration is up to 100 g of active ingredient per hectare.Evaluation of the growth of the cereals is made 21 days afterapplication. Compared with untreated controls, the new growth of thetreated plants is markedly reduced (60-90% of controls) and in someplants the diameter of the stalks is increased.

EXAMPLE 8 Growth Inhibition of Grasses

A mixture of the process Lolium perenne, Poa pratensis, Festuca ovina,Dactylis glomerata and Cynodon dactylon is sown in plastic dishes filledwith an earth/peat/sand mixture (6:3:1), in a greenhouse, and watered asrequried. The emergent grasses are cut back weekly to a height of 4 cmabove the soil and, about 50 days after sowing and 1 day after the lastcut, are sprayed with an aqueous spray mixture of a compound of theformula I. The concentration of test compound corresponds to a rate ofapplication of 100 kg per hectare. The growth of the grasses is assessedafter 21 days. Compared with untreated controls, the reduction in newgrowth effected by the compounds of formula I is in the region of10-30%.

EXAMPLE 9 Test of Selectivity in Preemergence Application

Seeds of dicot and monocot weeds and cultivated plants are sown in agreenhouse in pots of 11 cm diameter. Immediately afterwards the surfaceof the soil is treated with an aqueous dispersion or solution of thetest compound. Concentrations of 0.500, 0.125 and 0.030 kg a.i./ha areemployed. The pots are then kept in the greenhouse at 22°-25° C. and50-70% relative humidity. The test is evaluated after 3 weeks and theactivity is determined in accordance with the same rating as in Example3.

    ______________________________________                                        Activity                                                                      rate of application                                                           in kg a.i./ha Compound 123                                                    Test plant    0.500       0.125  0.030                                        ______________________________________                                        barley        5           7      8                                            wheat         8           9      9                                            Alopecurus myos.                                                                            2           3      6                                            Echinochloa c.g.                                                                            2           5      9                                            Rottboellia ex.                                                                             2           2      4                                            Cyperus escul.                                                                              3           3      4                                            Abutilon      2           3      7                                            Sida spinosa  2           3      4                                            Xanthium Sp.  2           2      3                                            Amaranthus ret.                                                                             2           2      2                                            Chenopodium Sp.                                                                             2           3      6                                            Ipomoea       1           2      4                                            Sinapis       2           3      7                                            Chrysanthe. leuc.                                                                           2           2      3                                            Galium aparine                                                                              2           5      8                                            Viola tricolor                                                                              2           2      3                                            ______________________________________                                    

EXAMPLE 10 Test of Selectivity in Postemergence Application

Following the test procedure of Example 6, a large number of plants aretreated with different concentrations of test compound. Evaluation ismade in accordance with the rating of Example 3.

    ______________________________________                                        Activity                                                                      rate of                                                                       application                                                                   in kg a.i./ha Compound 123                                                    Test plant    0.500       0.125  0.030                                        ______________________________________                                        wheat         8           9      9                                            Alopecurus myos.                                                                            2           3      5                                            Echinochloa c.g.                                                                            2           5      7                                            Rottboellia ex.                                                                             3           4      7                                            Cyperus escul.                                                                              3           4      6                                            Abutilon      2           2      4                                            Xanthium Sp.  1           1      2                                            Chenopodium Sp.                                                                             2           4      6                                            Ipomoea       2           3      3                                            Sinapis       2           2      2                                            ______________________________________                                    

What is claimed is:
 1. A compound selected from the group consisting ofa sulfonylurea of the formula: ##STR15## wherein R₁ is hydrogen, halo,or alkyl of 1 to 4 carbon atoms;R₂ is alkyl or alkoxy, each of 1 to 3carbon atoms, unsubstituted or substituted with 1 to 3 halogen atoms; R₃is halo, hydrogen, unsubstituted alkyl of 1 to 3 carbon atoms, alkyl of1 to 3 carbon atoms substituted with alkoxy of 1 to 4 carbon atoms orwith 1 to 3 halogen atoms, unsubstituted alkoxy of 1 to 3 carbon atoms,alkoxy of 1 to 3 carbon atoms substituted with methoxy, ethoxy, or 1 to3 halogen atoms, or --NR₄ R₅ in which R₄ is hydrogen or methyl and R₅ ishydrogen, methyl, ethyl, or methoxy; and Q is cyano or --COB in which Bis alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms; phenyl;phenyl substituted with cyano, nitro, halo, alkyl of 1 to 4 carbonatoms, alkoxy of 1 to 4 carbon atoms, alkythio of 1 to 4 carbon atoms,or haloalkyl of 1 to 3 carbon atoms; amino; alkylamino of 1 to 4 carbonatoms; or dialkylamino of 1 to 4 carbon atoms in each alkyl group; and Ais alkylene of 1 to 4 carbon atoms or alkenylene of 2 to 4 carbon atoms;and the alkali metal, alkaline earth metal, and organic amine saltsthereof.
 2. A compound according to claim 1 and selected from the groupconsisting of a sulfonylurea of the formula: ##STR16## wherein R₁ ishydrogen, halo, or alkyl of 1 to 4 carbon atoms;R₂ is alkyl or alkoxy,each of 1 to 3 carbon atoms, unsubstituted or substituted with 1 to 3halogen atoms; R₃ is halo, hydrogen, unsubstituted alkyl of 1 to 3carbon atoms, alkyl of 1 to 3 carbon atoms substituted with alkoxy of 1to 4 carbon atoms or with 1 to 3 halogen atoms, unsubstituted alkoxy of1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms substituted withmethoxy, ethoxy, or 1 to 3 halogen atoms, or --NR₄ R₅ in which R₄ ishydrogen or methyl and R₅ is hydrogen, methyl, ethyl, or methoxy; and Ais alkylene of 1 to 4 carbon atoms or alkenylene of 2 to 4 carbon atoms;and the alkali metal, alkaline earth metal, and organic amine saltsthereof.
 3. A compound according to claim 2 wherein R₁ is hydrogen,methyl or chloro; R₂ is methyl or methoxy; R₃ is methyl, methoxy,chloro, difuloromethoxy, ethoxy or dimethylamino; and A is alkylene of 1to 3 carbon atoms.
 4. A compound according to claim 1 and selected fromthe group consisting of a sulfonylurea of the formula: ##STR17## whereinR₁ is hydrogen, halo, or alkyl of 1 to 4 carbon atoms;R₂ is alkyl oralkoxy, each of 1 to 3 carbon atoms, unsubstituted or substituted with 1to 3 halogen atoms; R₃ is halo, hydrogen, unsubstituted alkyl of 1 to 3carbon atoms, alkyl of 1 to 3 carbon atoms substituted with alkoxy of 1to 4 carbon atoms or with 1 to 3 halogen atoms, unsubstituted alkoxy of1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms substituted withmethoxy, ethoxy, or 1 to 3 halogen atoms, or --NR₄ R₅ in which R₄ ishydrogen or methyl and R₅ is hydrogen, methyl, ethyl, or methoxy; and Bis alkyl of 1 to 4 carbon atoms, alkoxy of 1 4 carbon atoms; phenyl;phenyl substituted with cyano, nitro, halo, alkyl of 1 to 4 carbonatoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms,or haloalkyl of 1 to 3 carbon atoms; amino; alkylamino of 1 to 4 carbonatoms; or dialkylamino of 1 to 4 carbon atoms in each alkyl group; and Ais alkylene of 1 to 4 carbon atoms or alkenylene of 2 to 4 carbon atoms;and the alkali metal, alkaline earth metal, and organic amine saltsthereof.
 5. A compound according to claim 4 wherein R₁ is hydrogen,methyl or chloro; R₂ is methyl or methoxy; R₃ is methyl, methoxy,chloro, difluoromethoxy, ethoxy or dimethylamino; and A is alkylene of 1to 3 carbon atoms.
 6. A compound according to claim 5 wherein B ismethyl, methoxy, ethoxy, phenyl, methylamino or dimethylamino. 7.N-(2-Cyanomethoxy-phenylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaaccording to claim
 1. 8.N-(2-Cyanomethoxy-phenylsulfonyl)-N'-(4,6-dimethoxy-1,3,5-triazin-2-yl)-ureaaccording to claim
 1. 9.N-(2-Cyanomethoxy-phenylsulfonyl)-N'-(4-dimethylamino-6-methoxy-1,3,5-triazin-2-yl)ureaaccording to claim
 1. 10.N-(2-Ethxoycarbonylmethoxy-phenylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaaccording to claim
 1. 11.N-(2-Ethoxycarbonylmethoxy-phenylsulfonyl)-N'-(4,6-dimethoxy-1,3,5-triazin-2-yl)ureaaccording to claim
 1. 12.N-(2-Acetylmethoxy-phenylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaaccording to claim
 1. 13.N-(2-Benzoylmethoxy-phenylsulfonyl)-N'-(4,6-dimethoxy-1,3,5-triazin-2-yl)ureaaccording to claim
 1. 14.N-[2-(3-Methoxycarbonylallyloxy)phenyl-sulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaaccording to claim
 1. 15.N-(2-Methoxycarbonylmethoxy-5-methylphenylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea according to claim
 1. 16.N-(2-Cyanopropyloxy-phenylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaaccording to claim
 1. 17. A herbicidal and growth-regulating compositionwhich comprises an effective amount of at least one compound accordingto claim 1, together with a suitable carrier therefor.
 18. A method ofcontrolling undesired plant growth, which method comprises applyingthereto or to the locus thereof a herbicidally effective amount of acompound according to claim
 1. 19. A method of suppressing plant growth,which method comprises applying thereto or to the locus thereof aneffective amount of a compound according to claim
 1. 20. A methodaccording to claim 18 for selectively controlling weeds in crops ofcultivated plants which method comprises applying the compoundpre-emergence or post-emergence.
 21. A method according to claim 19 forsuppressing plant growth beyond the two-leaf stage which methodcomprises applying the compound pre-emergence.